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Tailscale raises $100M

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Re: Tailscale raises $100M

#151
post #116
post #41

As the founder of what some say is a competitor (ZeroTier) I'd like to congratulate the Tailscale team. We don't really see Tailscale as the competition. We see the competition as: (1) The old school castle and moat IT model that dominates at 99% of companies. If we can disrupt this then TS, ZT, and four other upstarts could all become billion dollar companies. Right now 1-2% of this market has been disrupted at most…

Agree with this Adam. Avery and the team at Tailscale are building a fantastic product and totally deserve the round and recognition, huge congratulations - we're super happy for them. In many ways they're also an ice-breaker for the zero trust overlay network architecture, which means they've got the most work to do. As the current top comment on this thread correctly notes, with huge investment comes the obligation…

What will happen over time is that as we disrupt old-school IT and re-introduce the idea that you can own your own compute (disrupting the everything-cloud model) the various participants in this new area will find niches in which their specific strengths and features shine the most. This always happens. Look at databases. There are like 10 decent sized database vendors for a reason, not to mention several paradigms: SQL, NoSQL, NewSQL, GraphQL, etc.

But if we don't succeed in disrupting the actual competition everyone fails.

At least that's how I look at this market.

Of course I'm also a mostly-follower of the "ignore your market peers, focus on the customer" philosophy. Your greatest competition is always your own shortcomings.

Re: Tailscale raises $100M

#152
post #94
post #9

With such a huge investment comes the obligation to eventually pay it back. Is this another one of my favourite tools going the way of Dropbox, 1Password and all other companies that were formed around what should be a platform feature, which took on way too large investment sums and were eventually forced to become the everything, losing sight of their core values? I sincerely hope not, but there's so much bad prece…

It’s a basic web UX over a built in Linux kernel feature There are Docker containerized apps that manage Wireguard too Maybe contribute to one and fret less about behavior of VC funded business and wondering if they’re actually respecting your privacy to accomplish finance goals

It handles a lot more than that, right? It does all of the key distribution and rotation which is a pain.

Re: Tailscale raises $100M

#153
post #39

For anyone else who wonders wtf tailscale is: > Tailscale is a VPN service that makes the devices and applications you own accessible anywhere in the world, securely and effortlessly. It enables encrypted point-to-point connections using the open source WireGuard protocol, which means only devices on your private network can communicate with each other. It seems to take care of key distribution, nat-traversal, authen…

Tailscale is one of the ways you can restore the end-to-end connectivity principle that IP introduced and that NAT destroyed.

Ah yeah, that makes sense.

Re: Tailscale raises $100M

#154
post #129
post #124

I was going to try TailScale but then it seemed the only option to do so as an individual was to login with a 3rd party cloud provider, which I in no way want tied into my networks. I gave up and just setup wireguard directly instead, I don't trust Tailscale either if that's their attitude towards privacy, it's permanently marred my vision of their product.

Yeah that's the biggest hangup I have, it just seems strange to rely on a third party login to be able to access something as important as a VPN. If my google account or whatever gets shut off for any reason I'd be pretty hosed.

Avery, co-founder at Tailscale, has some strong opinions about why SSO is sufficient for their product.

They wrote a bit about their thought process: Factors in authentication (2019), https://apenwarr.ca/log/20190114

> It seems to me that the above successful enrollment patterns all use one or more of the following techniques:

> A human authenticates you and issues you a token (usually in person).

> A short-distance, physical link (proximity-based authentication) like a biometric sensor, or USB or bluetooth connection.

> Delegation to an existing authenticator [SSO]...

> What people tend to miss... is that enrollment is necessary whether or not you send a push notification to the phone during login. The push notification is only secure if this specific browser instance is enrolled; but if this browser is enrolled, then the push notification adds no extra security... The enrollment was the security.

Fully expect them to ship u2f authenticators or sell them at tsCare shops!

Re: Tailscale raises $100M

#155
post #74
post #64

Earlier quoted context omitted.

That's gonna be exciting next time Slack is down.

I'd assume they have a fallback option to provide access.

It's a very safe assumption: we're just automating Tailscale ACLs. Tailscale admins (3 of us) can still come in and manually change them.

Re: Tailscale raises $100M

#156

Unfortunately despite claiming that they would, they've never allowed their iOS application to allow configuration of the control server (every other client they have released does). Maybe some more funding will allow them to focus on the client quality.

(Tailscale engineer here)

That's https://github.com/tailscale/tailscale/issues/1572 which we haven't given up on. It's just not done. We did it for macOS and we thought the same thing would've worked for iOS (they share ton of the same code) but it apparently didn't work.

The mobile apps have been a low priority thus far. We just recently hired some people to work on them, though.

The highest priority for them currently is fixing battery life (we do some dumb things when LTE + wifi are both available, and when using exit nodes, and some unnecessary heart beating that sucks on mobile) and then there's also a mobile app redesign (or just "design" coming).

We like Headscale and we're super glad that it exists. (they saved us some work by doing it first, as our control server wasn't in a releasable state) We keep Juan et al updated when there's protocol changes or things they can do. (e.g. recent https://github.com/juanfont/headscale/issues/552)

Re: Tailscale raises $100M

#157

How does it work for something like a security DVR where you can’t access the system itself? Is there an equivalent way to just access the network like a VPN?

Yes, you can set up one node as a gateway to the network, then access everything on that local network.

I use it this way to access devices that can't run the tailscale software.

Re: Tailscale raises $100M

#158

Tailscale has a fantastic product, I’ve been extremely happy from day one. If you’re waiting for a weekend to have a few hours to try out Tailscale, don’t, it takes 15 minutes to get every device you own up and running and talking. This is the lowest friction personal VPN to ever exist, and once you see how easy it is for your own devices, you’ll wish you had it at work. The biggest risk that this company has is that…

I’m pretty ignorant on this topic, but what are the benefits of having a personal VPN?

You can access your home network and any machines on it without exposing anything to the public internet. It's much safer to connect to my home network over a VPN than to expose all of the services to the public internet and hope they're all secure.

Re: Tailscale raises $100M

#159
post #63

Earlier quoted context omitted.

How has 1Password lost sight of its core values? Perhaps you refer to loss of local vaults? If so, they were never really a viable option for me - I needed the app syncing across multiple devices, including mobile, and doing so with a third party sync solution wasn't suitable.

For me, it was their switch to an Electron app. "High security" and "built from dozens of third party libraries and running on a browser" don't belong together.

The choice of tech stack for a desktop application seems like an interesting basis to claim a company has lost touch with its core values.

Re: Tailscale raises $100M

#160
post #38

Earlier quoted context omitted.

Tailscale will let you use any SAML or OIDC provider you like in the Enterprise plan (presumably because of the cost of supporting the long tail of nonsense IdPs will produce). (Disclosure: I'm a (small) investor via Latacora's sibling fund, Lagomorphic.)

Semi-related question: did Latacora or @tqbf ever open source their Go-based SAML IDP: https://twitter.com/tqbf/status/938501701526487040 (That tweet I think was a teaser saying it was coming. I subsequently looked for it a few times and never found it, but maybe plans changed, or maybe I just failed to find it).

Nope. It was pretty much just Thomas and Erin working on it, and I don't think it's operational. Sorry :(
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